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$418+ Cheap flights from Midland (MAF) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Midland to Caribbean

Keep the following information in mind while searching for Midland to Caribbean flight deals. Data was last updated September 15, 2025.

Round-trip from

$471
(Southwest)

One-way from

$418
(Southwest)

Popular in

July

Cheapest in

April

Average price

$526
From Midland Intl to Caribbean
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One-way flight from Midland Intl to Caribbean
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Highest demand for flights based on searches. 2% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midland to Caribbean

Cheapest flights from Midland to Caribbean
Explore the most affordable flight options available from Midland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/297:00 amMAF - SJU
1 stop7h 42mUnited Airlines
Thu 10/21:05 amSJU - MAF
2 stops10h 59mUnited Airlines
Deal found 9/14$485
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/245:00 amMAF - SJU
1 stop9h 42mUnited Airlines
Wed 10/12:00 pmSJU - MAF
1 stop8h 58mUnited Airlines
Deal found 9/12$502
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/225:35 amMAF - SJU
2 stops12h 10mSouthwest
Wed 9/2411:50 amSJU - MAF
2 stops10h 55mSouthwest
Deal found 9/14$519
This American Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2512:35 pmMAF - SJU
2 stops10h 02mAmerican Airlines
Mon 9/297:05 pmSJU - MAF
2 stops16h 42mAmerican Airlines
Deal found 9/13$530
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/25:11 pmMAF - SDQ
2 stops19h 30mDelta
Wed 11/58:49 pmSDQ - MAF
2 stops17h 04mDelta
Deal found 9/14$562
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:01 amMAF - SJU
1 stop7h 14mAmerican Airlines
Wed 9/246:10 amSJU - MAF
2 stops12h 37mAmerican Airlines
Deal found 9/14$575
This American Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/248:25 amMAF - SJU
2 stops8h 49mAmerican Airlines
Wed 10/16:10 amSJU - MAF
2 stops17h 54mAmerican Airlines
Deal found 9/12$585
This American Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/138:21 pmMAF - SJU
1 stop17h 04mAmerican Airlines
Mon 10/207:00 pmSJU - MAF
2 stops15h 43mAmerican Airlines
Deal found 9/13$602
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/227:00 amMAF - SJU
1 stop7h 42mUnited Airlines
Tue 9/231:05 amSJU - MAF
2 stops16h 07mUnited Airlines
Deal found 9/14$609
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:45 amMAF - SJU
2 stops10h 50mSouthwest
Sun 11/166:40 amSJU - MAF
2 stops11h 50mSouthwest
Deal found 9/13$640

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Midland to Caribbean that are best for you.

Fly from

Midland

Fly to

Caribbean

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 1/14

6:40 am-7:05 pm

2 stops10h 25m

San Juan Luis Munoz Marin Intl

Mon 1/26

5:40 am-4:15 pm

2 stops12h 35m

$478

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 9/29

5:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Fri 10/3

2:00 pm-9:58 pm

1 stop8h 58m

$485

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 9/29

12:36 pm-11:37 pm

2 stops10h 01m

San Juan Luis Munoz Marin Intl

Fri 10/3

7:05 pm-10:47 am

2 stops16h 42m

$485

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 1/14

12:24 pm-10:14 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Mon 1/26

6:45 am-9:19 pm

1 stop16h 34m

$490

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 9/24

5:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Wed 10/1

2:00 pm-9:58 pm

1 stop8h 58m

$502

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 3/10

8:33 pm-3:55 am

1 stop6h 22m

San Juan Luis Munoz Marin Intl

Wed 3/11

6:54 am-10:58 pm

1 stop17h 04m

$503

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Sun 11/2

5:11 pm-2:41 pm

2 stops19h 30m

Santo Domingo Las Americas

Wed 11/5

8:49 pm-11:53 am

2 stops17h 04m

$562

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Sat 2/28

8:32 pm-12:00 pm

2 stops14h 28m

Montego Bay Sangster Intl

Wed 3/4

11:55 am-10:16 pm

1 stop11h 21m

$655

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 12/17

11:00 am-9:30 pm

2 stops8h 30m

$418

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 12/24

6:15 am-6:35 pm

2 stops10h 20m

$448

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 14 results
1
2

Best time to book a flight from Midland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Midland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Midland to Caribbean

What is the cheapest month to book a flight from Midland to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Midland to Caribbean (average of $254). Flying from Midland to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MAF to CB?

Find hourly flight availability from Midland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Midland to Caribbean as you normally would.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated September 15, 2025.
Read through reviews of airlines operating flights from Midland to Caribbean, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Midland to Caribbean?

    Most people fly from Midland Intl (MAF) if they book a flight from Midland to Caribbean. Midland Intl is conveniently located just 8.2 mi from Midland’s city center.

  • How long is the flight from Midland to Caribbean?

    Airlines like Southwest, United Airlines, and American Airlines fly from Midland to Caribbean in about 9h 42m. The time it takes to get you to your destination can typically vary by up to 43m. The distance from Midland to Caribbean is about 2432 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Midland to Caribbean one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $418. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Midland to Caribbean for a low price.

  • What are the most popular routes from Midland to Caribbean?

    The most popular flight routes from Midland to Caribbean are Midland Intl - San Juan Luis Munoz Marin Intl, Midland Intl - Montego Bay Sangster Intl and Midland Intl - Oranjestad Reina Beatrix.

  • Can I find deals for flights from Midland to Caribbean that include hotel bookings?

    Yes. In addition to deals on Midland to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midland to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midland to Caribbean.

  • Can I find deals for business class flights from Midland to Caribbean?

    Yes. Cheapflights offers flight deals from Midland to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Midland to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Midland to Caribbean (average of $254). Flying from Midland to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Midland to Caribbean

Discover the top 3 airlines that operate flights from Midland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$370Average$570FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$380Average$922FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$513Average$544FlexibilityNo cancel feeOn-time63%

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